Non-heme diiron active sites are prevalent in metalloenyzmes throughout Nature. Synthetic analogues of these active sites have furthered our understanding of the fundamental principles that control the reactivity of these enzymes. The proposed study outlines a general strategy for the synthesis of novel, sterically encumbered dinucleating nitrogen ligands for use in the creation of synthetic analogues of these diiron active sites, in this case the active site of the methane-oxidizing enzyme methane monooxygenase (MMO). The implications of this work span from knowledge gained about these dimetallic centers to the development of small molecule catalysts for hydrocarbon oxidation that could impact the health field concerning the production of fine chemicals and pharmaceuticals. The research proposed involves the design of a general strategy for the synthesis of a structurally diverse set of dinucleating nitrogen ligands. The structure of these bischelating ligands will be based upon two heterocyclic amine functionalities, the indoline and isoindoline. The power of palladium catalyzed carbon-carbon bond forming processes will be employed to assemble these ligands in short order and install these chelating moieties inside sterically demanding environments, The carbon framework that links the two monodentate amine functionalities will be readily varied, resulting in the production of a diverse set of ligands. The synthetic strategy will enhance diversity by generating multiple ligand sets from the same intermediate. Molecular modeling concludes that controlling the relative stereochemistry of the chiral C2 symmetric and meso diamines produced will control the steric environment and coordination geometry of this novel ligand set.